Historic Route 66 Kid friendly Vacations
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Top Kid friendly vacation packages in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥419,698, price is now ￥342,926 per person
￥342,926
per person
Mar 15 - Mar 19
just found
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
The room was boring thought it would be cleaner updated for the price best part was the view
Reviewed on Jan 24, 2026
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See all available trips from Osaka to Historic Route 66
View all trips5* Kid friendly vacations in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥419,698, price is now ￥342,926 per person
￥342,926
per person
Mar 15 - Mar 19
just found
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
The room was boring thought it would be cleaner updated for the price best part was the view
Reviewed on Jan 24, 2026
Don't see what you're looking for?
See all available trips from Tokyo to Historic Route 66
View all trips3 Night Kid friendly vacations in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥316,616, price is now ￥269,518 per person
￥269,518
per person
Mar 11 - Mar 14
found 16 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Beautiful room, great location. Will definitely stay there again.
Reviewed on Jan 28, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥360,070, price is now ￥301,847 per person
￥301,847
per person
Mar 11 - Mar 14
found 16 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
The room was boring thought it would be cleaner updated for the price best part was the view
Reviewed on Jan 24, 2026
The Peninsula Chicago
Downtown Chicago
Price was ￥385,894, price is now ￥339,514 per person
￥339,514
per person
Mar 11 - Mar 14
found 16 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
The best hotel ! Always pleasant to stay !
Reviewed on Jan 27, 2026
Don't see what you're looking for?
See all available trips from Tokyo to Historic Route 66
View all trips4 Night Kid friendly vacations in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥419,698, price is now ￥342,926 per person
￥342,926
per person
Mar 15 - Mar 19
just found
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
The room was boring thought it would be cleaner updated for the price best part was the view
Reviewed on Jan 24, 2026
Don't see what you're looking for?
See all available trips from Osaka to Historic Route 66
View all trips* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
